The Social Expert is a character with people skills, especially when dealing with large groups of people. He can recognize the social patterns in a group, figure out people's motivations, and know who the person in charge is. The Social Expert can identify who's manipulatable, who's a manipulator, and who's neither. The Social Expert can make himself likable even to his enemies, and is normally clever enough not to make very many of them.

Examples:

Izaya Orihara from Durarara!!, aside from being a complete Troll and Manipulative Bastard and claiming to "love humanity" (except for Shizuo), also performs his own social experiments, such as encouraging depressed people contemplating suicide to do so, or making suicide pacts with them and then revealing he was just kidding and thinks they are idiots, just to see if they really will commit suicide or not. Or paying people to kidnapping someone, and then paying someone else to rescue them, just to see how they'll react. Yes, Izaya is a dick.

Both Lelouch Lamperouge and his older brother, Prince Schneizel, in Code Geass.

Ukraine from Hetalia is a Nice Girl version. She's the member of the Slavic corner with the best social skills, and tends to get along fine with other nations while Russia and Belarus are... well, themselves.

Lex Luthor. His people skills allow him to both keep up his Villain with Good Publicity status as well as make sure his covert operations are in order. He is so good at this he is one of the few people who can keep the Joker in check during a villain team up.

Livewires had a character called "Social Butterfly", whose talents lay in social situations.

Storm Watch PHD had Gorgeous, a beautiful woman with a talent for manipulating men. She served as the team's profiler.

In The Hustler, this is Bert Gordon's most important skill as a Manipulative Bastard; he can quickly size up someone and identify their innermost weaknesses. He's so good that even after losing $18,000 to Eddie Felton in a 25-hour marathon session of pool, Minnesota Fats cheerfully agrees to keep playing just because Bert identified him as a "loser" — and then proceeds to win it all back.

None are quite so skilled or dangerous as Littlefinger, who set the War of Five Kings in motion with just a few carefully chosen words.

Harry Potter: By the time you realize the full breadth of Dumbledores' planning and manipulation in book seven, he looks like a full-on Magnificent Bastard.

The Picture of Dorian Gray has Lord Henry Wotton. Everything bad that happens during the story could be traced back to his words and the way he uses them.

Rosario Blancanales takes this role in the Heroes "R" Us group Able Team, and it's the reason for his nickname 'The Politician'.

Twilight: Jasper was such a social expert as a human, he became an Empath with emotion manipulation powers as a vampire.

Lloyd Henreid in The Stand becomes the defacto face and diplomat of Las Vegas because of his surprisingly good people skills. Just the fact that he's still alive after traveling and working with psychos like Andrew "Poke" Freeman and Randall Flagg is proof.

Grifter Sophie Deveraux (or whatever her real name is) from Leverage. Her role on the team is to manipulate the mark with multiple "roles" that she plays, but often someone else needs to be sent in for one reason or another, and she'll coach them by reading the players and describing what she does and why.

Special Agent Seeley Booth on Bones, who often relies on his 'gut' to solve crimes and is referred to as the 'people person' because of his natural intuitive insights and ability to read people well.

One of the main unique character quirks of the Second Doctor in Doctor Who. He can walk into any situation and immediately map out the social dynamics by observing their body language and interactions, approach whoever is almost certain to know more than everyone else, and then instantly figure out what they mean by the fact that they're lying about his questioning. "Power of the Daleks" is a spectacular example, where he effortlessly bluffs his way into the upper social circle of an Earth colony by pretending to be an examiner from Earth, and immediately makes a whole map of who's trying to overthrow who just by watching the politicians' facial expressions as they answer his trivial questions, while still recovering from temporary confusion caused by his first regeneration.

Leela. The Doctor is better at reading people than he pretends to be, but Leela's warrior training and unusual intelligence enables her to read and understand body language and facial nuance far better than he ever could. This is especially prominent in "The Robots of Death", which she spends a few steps ahead of him and a giant leap ahead of the people who actually are supposed to be solving the mystery the whole time.

Many games use a social/mental/physical skill/ability distribution, including:

Anything White Wolf makes.

Exalted has a threefold division between social skills, mental skills, and physical skills. Any character with high social skills is a social expert. Among the Solars, members of the Zenith and Eclipse castes have the greatest talent in this area.

Dresden Files goes one step further, where you can fully engage in social combat, allowing you to browbeat your opponents into submission, with social skills.

Shadowrun. At least one character in the PC group needs to have good social skills to deal with the various NPCs the group will encounter. They should have high Charisma, good Etiquette skills and possibly cyberware/bioware that enhances those qualities (e.g. tailored pheromones). Such a person may be called "The Face" of the group.

Mike Thorton, the protagonist from Alpha Protocol, is described by his boss as someone who knows how to manipulate people to get what he wants, and this is reflected in the conversation system. The conversational stances that Mike takes may have nothing to do with what he feels, and can drive people to friendship or enmity. according to his objectives.

Terezi in Homestuck is the most talented manipulator of the series thanks to being the Social Expert, contrasted with Vriska who relies on more direct Psychic Powers. Crowbar of The Felt is so good with people that he was able to win over Caliborn, the most unpleasant character in the story bar none, over the course of a single conversation.

Elan in The Order of the Stick is a story-telling expert because his role is the party bard. This makes him able to predict the actions and motivations of almost everyone involved. His father is however far more experienced in the role.

Belkar is a more focused example. Multiple times he's shown he knows exactly what to say to someone, whether it be a mentally-unstable paladin, a grieving friend or a man who's just got a taste for violence. He isn't nice about it, but he can get them to do what he wants.

Azula's actually an interesting case. She can accurately predict the movements, motivations and operatonal methods of virtually anyone she encounters. This makes her an incredibly dangerous. She can also be very charismatic at times (just look at her aforementioned take down of Long Feng. But when it comes to every day, basic social interaction, she fails. Completely.

Trent Lane in Daria, despite a personality so laid back that his communiques are seldom and brief, is often able to identify moments of mounting tension between his sister Jane and her titular best friend. A few times throughout the series he tries to drop subtle (well, slightly subtle) hints that steer the girls towards peaceful resolution. Ironically, he seems pretty oblivious to Daria's long-standing crush on him up until she finally gets over it, at which point he gives her a quiet apology for letting her down when she was counting on him while subtly explaining exactly why they would never work as a couple — without one of both of them giving up some core facet of themselves to make the other happy.

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